US10577561B2 - Process for obtaining a scented extract of fresh flowers and/or leaves using natural solvents - Google Patents

Process for obtaining a scented extract of fresh flowers and/or leaves using natural solvents Download PDF

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US10577561B2
US10577561B2 US13/996,693 US201113996693A US10577561B2 US 10577561 B2 US10577561 B2 US 10577561B2 US 201113996693 A US201113996693 A US 201113996693A US 10577561 B2 US10577561 B2 US 10577561B2
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alcoholic
flowers
leaves
extract
scented
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US20130338241A1 (en
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Sophie Lavoine-hanneguelle
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Charabot SA
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Charabot SA
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/025—Recovery by solvent extraction
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute

Definitions

  • the invention relates to a process for obtaining a scented extract from fresh flowers, flowery tops and/or leaves using a combination of natural solvents, the extracts thus obtained and the uses of same.
  • Fresh flower and/or leaf extracts are used in particular in perfumes, cosmetics and flavors, and more specifically those of fragrant flowers or leaves such as, for example, jasmine, mimosa, rose, bitter orange, or basil.
  • An extraction is performed using volatile non-polar solvents obtained from petrochemistry, such as hexane, benzene or petroleum ether.
  • volatile non-polar solvents obtained from petrochemistry, such as hexane, benzene or petroleum ether.
  • the water from the plants is then decanted, and the solvent containing the fragrance is concentrated under vacuum to produce the concrete.
  • the floral products currently offered on the market are either essential oils, concretes obtained using non-polar petroleum solvents or more commonly absolutes obtained from the retreatment with supercritical CO 2 or alcohol washes of such concretes.
  • composition of the products obtained by such processes is substantially different from the raw material, and the respective scent is not comparable to that of the fresh flower.
  • Non-polar solvents extract in particular, fatty materials, which confer fatty notes on the concretes.
  • the need for a petroleum solvent does not comply with the Cosmebio charter.
  • Document EP0309339 is also known, which more specifically discloses a process for preparing a scented jasmine flower composition obtained by hydrolysis of the isolated compounds and in particular precursors, by extracting flowers with an aqueous or hydro-alcoholic polar solvent.
  • a problem to be solved by the invention is that of implementing a process for obtaining a scented extract from fresh flowers and/or leaves by a combination of natural solvents, not obtained from petrochemistry, and that complies with the Cosmebio charter, which defines the basic principles of ecological and biological cosmetics according to specifications certified by Ecocert.
  • Such a process is easy to implement, efficient, and the scented extracts thus obtained have a scent substantially similar to that of the fresh flower, different from the traditional perfumery standards.
  • the invention therefore first relates to a process for obtaining a scented extract from fresh flowers, flowering tops, and/or leaves of a moist plant including the following steps, wherein: a) the flowers, flowering tops and/or leaves of the plant are picked; b) said freshly cut flowers, flowering tops, and/or leaves are infused in at least one bath including an alcoholic solvent, at a temperature below 50° C., so as to obtain an alcoholic mixture; c) said alcoholic mixture is filtered so that an alcoholic floral infusion is recovered; and d) a supercritical CO 2 extraction of the alcoholic floral infusion is performed to obtain said scented extract, this scented extract being titrated with at least 75% alcohol.
  • the invention secondly relates to an extract prepared by the process according to the invention.
  • the invention thirdly relates to the method of providing an extract according to the invention to prepare a perfume, a perfumed dilution alcohol, a perfumery ingredient, a food flavoring or in the composition of a cosmetic product.
  • FIG. 1 shows a floral diagram wherein the scent of a hexane jasmine flower extract is compared with that of an extract obtained according to the process according to the invention
  • FIG. 2 shows a floral diagram wherein the scent of a hexane mimosa flower extract is compared with that of an extract obtained according to the process according to the invention.
  • the process according to the invention is implemented so as to obtain a scented extract from fresh flowers, flowering tops, and/or leaves, particularly fragile, from a moist plant.
  • a moist or fresh plant is a living organism forming part of the plant kingdom, which comprises at least 70% water by weight of its total weight, conventionally around 85% water, before or after loss to desiccation in particular associated with picking.
  • jasmine As a non-limiting example of fragile fresh flowers, flowering tops and/or leaves according to the invention, it is possible to cite jasmine and in particular among more than 200 species, Jasminum grandiflorum, Jasminum officinale, Jasminum odoratissimum, Jasminum sambac, Jasminum auriculatum, Jasminum flexile , mimosa, rose, tuberose, genet, bitter orange, carnation, violet, verbena , linden, chamomile, basil leaf, coriander leaf, frangipani, tiaré, gardenia , marigold, French marigold, narcissus , hyacinth, daffodil, lily, magnolia , lily of the valley, ylang-ylang, osmanthus , lilac, honeysuckle or geranium.
  • the important parts of the plant are picked, namely the flowers, flowering tops and/or leaves.
  • Such freshly picked flowers, flowering tops and/or leaves are very fragile and can be preserved as is only for a short time, at most several hours, for example 12 hours, and will preferably be used within 3 hours after picking to prevent degradation and loss of a large part and sometimes all of their scented, and primarily fragrant, qualities.
  • jasmine flowers degrade 3 hours after being picked, and mimosa or tuberose flowers can be preserved as is for up to 12 hours.
  • said freshly picked flowers, flowering tops and/or leaves are infused in at least one bath containing an alcoholic solvent, at a temperature below 50° C., so as to obtain an alcoholic mixture.
  • a natural alcohol is used, chosen from methanol, ethanol, propanol 1, 2-propanol, butanol, isobutanol, pentanol, isoamylic alcohol and preferably ethanol which has a lower boiling point (except for methanol) and which is much less toxic than methanol in particular.
  • the flowers, flowering tops and/or leaves are preferably infused in the alcoholic solvent at room temperature, i.e. at a temperature between 15 and 35° C.
  • the duration of the infusion step according to the invention can be up to several hours, for example 12 hours, and will have an influence on the olfactory profile of the extract.
  • the duration of the infusion according to the invention was optimized and is between around ten minutes to around two hours, a time necessary and sufficient for extracting the scented molecules collected in the primary scented alcohol extract according to the invention.
  • the flowers, flowering tops and/or leaves are steeped in the alcoholic solvent and can be gently stirred.
  • the infusion is produced by circulating the solvent in a closed circuit, i.e. the solvent is circulated over the flowers, flowering tops and/or leaves so as to create movement in the extractor, without breaking in particular the petals, and avoiding areas of saturation of the solvent at the periphery of the petals.
  • the stirring thus provides less saturated solvent, which in turn will perform the extraction.
  • infusions in a plurality of concomitant or sequential baths, depending on the quantity of flowers and/or leaves to be treated.
  • the flowers and/or leaves are advantageously passed multiple times through the same alcohol bath in order to saturate it, for example up to 5 passes, enabling the primary alcoholic extract to be concentrated.
  • This is more economical in terms of volumes to be transported and subsequently treated with supercritical CO 2 .
  • the flowers, flowering tops and/or leaves are drained, without being crushed, and the alcoholic mixture thus obtained is filtered so as to recover an alcoholic floral infusion capable of being kept cool at a temperature of around 4 to 10° C. for a period of one day to a number of months.
  • Such an alcoholic floral infusion according to the invention is a product that is possibly colored, with an especially high water and sugar content, and titrated with at least 45% alcohol.
  • This infusion step according to the invention is essential because it makes it possible to preserve, for several weeks, at between 4 and 10° C. in the form of an alcoholic floral infusion, an extract of fresh fragile flowers and/or leaves that would not stay fresh, and without altering the scented qualities. Indeed such fresh flowers and/or leaves must be used quickly after being picked to prevent drying and loss of all of their scented and primarily fragrant qualities.
  • the process according to the invention also comprises a step wherein the alcoholic floral infusion is kept fresh at a temperature of around 4 to 10° C. for a period of between 1 day and several months, for example 12 or even 24 months.
  • the process according to the invention is easy to implement and limits the time constraints. Moreover, the process according to the invention makes it possible to guard against complex logistics associated with the bulk of the extraction equipment and the fact that the plants containing it are often not located near the harvesting sites. Instead, the alcoholic floral infusion obtained according to the invention can easily be transported to sites where it will undergo the refining necessary for obtaining a scented extract smelling of fresh flowers and/or leaves according to the invention.
  • a supercritical CO 2 extraction of the alcoholic floral infusion is performed in order to obtain said scented extract.
  • this scented extract obtained according to the invention is titrated with at least 75% alcohol.
  • the supercritical CO 2 extraction process is known.
  • the CO 2 In the supercritical state, namely more than 74 bars and 31° C., the CO 2 has very specific properties and can be used as a natural extraction solvent.
  • the fluid obtained is characterized by a high diffusivity (on the order of that of gases), which makes it suitable for diffusion, and a high density, which makes it highly suitable for transport and extraction.
  • the supercritical CO 2 extraction step according to the invention can be performed in static mode or in dynamic mode.
  • CO 2 is preferably used at a pressure of between 130 and 200 bars and at a temperature of between 35 and 55° C., even more preferably at 150 bars and 45° C., at counter-current, and is particularly suitable for obtaining a clear, limpid and stable scented extract of fresh flowers and/or leaves largely free of sugars, colorants, water and titrated with at least 75% alcohol.
  • the process according to the invention also comprises a step wherein the scented extract obtained after extraction with supercritical CO 2 is concentrated as is, under vacuum by gentle heating below 60° C., or on a substrate such as natural oil, Shea butter, natural glycerin or a natural fragrant molecule such as natural benzyl acetate.
  • the process according to the invention gives yields at least similar to those obtained with the traditional processes for obtaining an essential oil or an absolute from these same flowers, and greater than those obtained by extraction directly on the flowers with supercritical CO 2 .
  • mass yields equivalent to 2 kg of flowers per kg of extract are obtained.
  • the table below shows, with measurements performed in gas chromatography by the applicant, the composition of an extract obtained according to the process according to the invention, using 750 kg of Jasminum grandiflorum flowers picked in the Maritime Alps from August to October 2010. Two hours after being picked, these flowers were infused, gently stirred, in natural ethanol at 25° C. for 20 minutes, with the flower/ethanol ratio being 1:1 by weight. Then, the flowers were drained, without being too crushed, and rinsed. The alcoholic floral infusion was then filtered and packaged for 2 to 3 months pending the supercritical CO 2 extraction. Finally a supercritical CO 2 extraction of the alcoholic floral infusion was performed at 45° C. and 150 bars for 20 minutes.
  • the scented extract thus obtained according to the invention was then partially concentrated under vacuum at low temperature (35° C.). To this effect, in the table below, the composition of the scented extract according to the invention thus obtained was compared with that of a traditional absolute obtained by hexane extraction from the same flower harvest and diluted to 10% in alcohol.
  • This table shows, on the basis of the results obtained, differences in composition between a jasmine flower extract obtained according to the process according to the invention and a hexane absolute of these same flowers.
  • the jasmine flower extract obtained according to the process according to the invention comprises, in particular, in significant amounts, more methyl jasmonate and maltol than the hexane absolute does, and contains phenylacetaldehyde, whereas the hexane absolute does not contain it.
  • the jasmine flower extract obtained according to the process according to the invention comprises, in a significant amount, less eugenol than the hexane absolute does, and does not comprise geraniol or indole in this production.
  • the extract obtained according to the process according to the invention does not contain, for example, geraniol or phenyl-2-ethanol.
  • compositions between the extracts are characterized by substantially different scents.
  • the applicant performed a scent test using 8 professionals in order to compare the scents of the 2 jasmine flower extracts mentioned in the table above.
  • This floral diagram shows, on the basis of the results obtained, differences in scent between the 2 extracts characterized by the differences in composition mentioned in the table above.
  • the extract obtained according to the process according to the invention has fine floral scents due, in particular, to the jasmonates as well as a sweet, fruity honey scent due, in particular, to the maltol. Also, very vegetal notes are observed, of tea hay, characteristics of the scent of the local country, jasmine flowers and bushes with the extract obtained according to the process according to the invention, which is not the case with the hexane extract. However, the absence of indole and waxes in this extract according to the invention makes it possible to limit the powerful animal and fatty floral scent characteristic of these compounds, found only in the hexane extract.
  • the extract obtained according to the process according to the invention using jasmine flowers is in the form of a very pale yellow to yellow, limpid, mobile, transparent liquid, and has a native fresh flower scent.
  • a concentrate is obtained that is in the form of a very powerful brown-green liquid or paste with jasmine, vegetal, fruity, honey notes.
  • the table below shows, with measurements performed in gas chromatography by the applicant, the composition of an extract obtained according to the process according to the invention using 2 kg of mimosa flowering branches picked in the Tanneron Massif in March 2010. Four hours after being picked, these mimosa flowering branches were infused in 6 kg of natural ethanol circulating at 25° C. for 2 hours, with the mimosa flowering branch/ethanol ratio being 1:3 by weight. The alcoholic floral infusion was then filtered and packaged pending the supercritical CO 2 extraction for 3 weeks. Finally, a supercritical CO 2 extraction of the alcoholic floral infusion was performed at 45° C. and 150 bars for 20 minutes.
  • the scented extract thus obtained according to the invention was then concentrated under vacuum, iced and filtered, for a soluble concentrate yield of the flower of 0.40% in this trial.
  • the composition of the scented extract according to the invention thus obtained is compared in the table below with that of a traditional absolute obtained by hexane extraction from the same harvest of mimosa flowering branches and diluted to 10% in alcohol.
  • This table shows, on the basis of the results obtained, a notable variation in the chemical balance between the most volatile compounds (the most scented) and the heaviest compounds to the advantage of the mimosa flowering branch extract (0.68) obtained according to the process according to the invention with respect to the classic extract (hexane then ethanol) (0.12). Composition differences are thus observed between this extract obtained in the process according to the invention and the absolute, and in particular the mimosa flowering branch extract obtained according to the process according to the invention comprises, in a significant amount, more heptadec-8-ene than the hexane absolute, and comprises two times less lupenone and lupeol in this production.
  • composition differences between the extracts are characterized by substantially different scents.
  • the applicant performed a scent test with 8 professionals in order to compare the scents of the 2 mimosa flowering branch extracts mentioned in the table above.
  • This floral diagram shows, on the basis of the results obtained, differences in scent between the 2 extracts characterized by the composition differences mentioned in the table above.
  • the extract obtained according to the process according to the invention has fine floral scents characteristic of methyl anisate, very vegetal, powdery and faithful to the scent of mimosa.
  • the hexane absolute has a powerful green, fatty (cis-3-hexenol) floral note, powerful head note with a weaker and less persistent background note.
  • the extract obtained according to the process according to the invention based on mimosa flowering branches is in the form of a mobile alcoholic liquid titrated at more than 85% by weight of alcohol, transparent yellow and with a very light, gentle honey scent, characteristic of fresh mimosa flowers.
  • a concentrate is advantageously obtained that can be iced and filtered, and then becomes pasty, darker, olive green, its odor intensifying with floral, honey and vegetal notes.
  • the process according to the invention thus makes it possible to obtain a scented fresh flower and/or leaf extract using natural solvents, not obtained from petrochemistry, and which complies with the Cosmebio charter that defines the basic principles of ecological and organic cosmetics according to specifications certified by Ecocert.
  • the process according to the invention makes it possible to obtain scented extracts that are faithful to the scent of natural fresh flowers, and that are different from the traditional perfumery standards.
  • the invention relates to an extract prepared by the process according to the invention.
  • the extracts thus obtained according to the process according to the invention can be used as is as a perfume, or a perfumed dilution alcohol, or a perfumery ingredient.
  • Such extracts can advantageously replace the neutral dilution alcohol of a scented water or a perfume. They can also be used in concentrated form.
  • the extract obtained after supercritical CO 2 extraction is a natural alcohol delicately performed with the plant matter such as the jasmine flower, a limpid liquid that can be used as is.
  • the extract has not been degraded by heating, and the scent is very faithful to that of the plant.
  • the extract according to the invention is stable during storage, whereas the absolute, for example the jasmine absolute, deposits wax over time (sediment), influencing its appearance and even its scent.
  • the extract according to the invention can also be used as a food flavoring or in the composition of a cosmetic product.
  • compositions intended for topical use in particular on the skin such as a gel, a cream, a milk, a lotion, an oil, a shampoo or a soap can be cited.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
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  • Extraction Or Liquid Replacement (AREA)
  • Cosmetics (AREA)
US13/996,693 2010-12-23 2011-12-22 Process for obtaining a scented extract of fresh flowers and/or leaves using natural solvents Active 2033-04-01 US10577561B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1005098A FR2969656B1 (fr) 2010-12-23 2010-12-23 Procede pour l'obtention d'un extrait odorant de fleurs et/ou feuilles fraiches par des solvants naturels
FR1005098 2010-12-23
PCT/FR2011/000674 WO2012085366A1 (fr) 2010-12-23 2011-12-22 Procede pour l'obtention d'un extrait odorant de fleurs et/ou feuilles fraiches par des solvants naturels

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US20130338241A1 US20130338241A1 (en) 2013-12-19
US10577561B2 true US10577561B2 (en) 2020-03-03

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US (1) US10577561B2 (fr)
EP (1) EP2655583B1 (fr)
JP (2) JP2014507502A (fr)
ES (1) ES2538398T3 (fr)
FR (1) FR2969656B1 (fr)
IN (1) IN2013MN01207A (fr)
TN (1) TN2013000266A1 (fr)
WO (1) WO2012085366A1 (fr)

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CN105168101A (zh) * 2015-10-24 2015-12-23 黄宇松 一种花香沐浴露及其制备方法
CN106334338A (zh) * 2016-11-19 2017-01-18 王芹 一种用于动植物原料的单级洗脱装置及其方法和用途
CN109135931A (zh) * 2018-09-04 2019-01-04 海南大学 一种红睡莲精油提取方法
CN109453091B (zh) * 2019-01-02 2021-08-24 广东美宝化妆品有限公司 一种基于复合鲜花提取液的香水及其制备方法
FR3097765B1 (fr) 2019-06-28 2021-07-23 Oreal Extrait de rosier
FR3110417B1 (fr) * 2020-05-19 2023-03-17 Int Flavors & Fragrances Inc Absolues pour leur utilisation cosmétique
FR3117868A1 (fr) 2020-12-17 2022-06-24 L'oreal Utilisation d’un extrait de rosier comme actif dépigmentant
EP4035653A1 (fr) 2021-01-29 2022-08-03 Chanel Parfums Beauté Extrait huileux de fleurs de gardenia jasminoides et compositions cosmétiques le comprenant
CN115428980B (zh) * 2022-10-12 2023-05-09 茂名华美实业有限公司 一种适用于加热不燃烧型烟草制品的烟用香精

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EP2655583A1 (fr) 2013-10-30
JP2014507502A (ja) 2014-03-27
US20130338241A1 (en) 2013-12-19
FR2969656A1 (fr) 2012-06-29
EP2655583B1 (fr) 2015-03-11
JP6714798B2 (ja) 2020-07-01
ES2538398T3 (es) 2015-06-19
FR2969656B1 (fr) 2013-01-04
WO2012085366A1 (fr) 2012-06-28
TN2013000266A1 (fr) 2014-11-10

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